US10023658B2 - Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof - Google Patents
Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof Download PDFInfo
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- US10023658B2 US10023658B2 US15/124,827 US201515124827A US10023658B2 US 10023658 B2 US10023658 B2 US 10023658B2 US 201515124827 A US201515124827 A US 201515124827A US 10023658 B2 US10023658 B2 US 10023658B2
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- hyaluronic acid
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- conjugates
- acid oligomer
- oligomer
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- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 64
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 56
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 150000003839 salts Chemical class 0.000 title claims abstract description 17
- 239000000758 substrate Substances 0.000 claims abstract description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 150000004676 glycans Chemical class 0.000 claims description 10
- 229920001282 polysaccharide Polymers 0.000 claims description 10
- 239000005017 polysaccharide Substances 0.000 claims description 10
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 235000011054 acetic acid Nutrition 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- -1 hyaluronic acid disaccharide Chemical class 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- QHXLIQMGIGEHJP-UHFFFAOYSA-N boron;2-methylpyridine Chemical compound [B].CC1=CC=CC=N1 QHXLIQMGIGEHJP-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 230000004071 biological effect Effects 0.000 abstract description 7
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000005647 linker group Chemical group 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 0 *C(C([3*])O)C(*)C([4*])/C=N/C[5*]C/N=C/C.*C(C([3*])O)C(*)C([4*])/C=N/C[5*]CNCC.*C1C([3*])OC(NC[5*]C/N=C/C)C([4*])C1*.*C1C([3*])OC(NC[5*]CNCC)C([4*])C1* Chemical compound *C(C([3*])O)C(*)C([4*])/C=N/C[5*]C/N=C/C.*C(C([3*])O)C(*)C([4*])/C=N/C[5*]CNCC.*C1C([3*])OC(NC[5*]C/N=C/C)C([4*])C1*.*C1C([3*])OC(NC[5*]CNCC)C([4*])C1* 0.000 description 13
- 238000000914 diffusion-ordered spectroscopy Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 10
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 description 9
- 239000012265 solid product Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 229940099552 hyaluronan Drugs 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 7
- 238000006268 reductive amination reaction Methods 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000002016 disaccharides Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- ALHNLFMSAXZKRC-UHFFFAOYSA-N benzene-1,4-dicarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C=C1 ALHNLFMSAXZKRC-UHFFFAOYSA-N 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 150000004044 tetrasaccharides Chemical class 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- PIGCSKVALLVWKU-UHFFFAOYSA-N 2-Aminoacridone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3NC2=C1 PIGCSKVALLVWKU-UHFFFAOYSA-N 0.000 description 1
- WWTUGGKURBFNAE-UHFFFAOYSA-N COC1OC(CO)C(O)C(OC2OC(C(=O)O)C(OC)C(O)C2O)C1NCC=O Chemical compound COC1OC(CO)C(O)C(OC2OC(C(=O)O)C(OC)C(O)C2O)C1NCC=O WWTUGGKURBFNAE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910020889 NaBH3 Inorganic materials 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 210000002901 mesenchymal stem cell Anatomy 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Definitions
- the invention relates to conjugates of hyaluronic acid or a salt thereof, method of preparation thereof and use thereof.
- Hyaluronic acid is a glycosaminoglycan composed of two repeating saccharidic cycles of ⁇ -(1,3)- D -glucuronic acid and ⁇ -(1,4)-N-acetyl- D -glucosamine.
- This very hydrophilic polysaccharide is water-soluble in the form of a salt within the whole pH range. It forms a part of connective tissues, skin, synovial fluid of joints, it plays an important role in a number of biological processes such as hydration, proteoglycan organisation, cell differentiation, proliferation and angiogenesis.
- the native hyaluronic acid is a linear polysaccharide which is degraded in the organism quite fast.
- the first convincing attempts of preparation of hyaluronan having a branched structure were described in 2008 by Toemmeraase K. (WO 2008/014787). It concerns bonding of the amino group of deacetylated hyaluronan having a higher molecular weight with the ending anomeric center of hyaluronan oligomer by means of reductive amination.
- the authors of another patent document
- an amino group is generated in the position 6 of the glucosamine part of the HA oligomer, which amino group then reacts at mild conditions with NHS esters of carboxylic acids bound to carbon nanotubes.
- Bonding of the ending anomeric center of hyaluronan having a lower molecular weight by means of a diamino or polyamino linker using the reductive amination is disclosed by Xu (WO 2007/101243).
- the resulting substrates were used for encapsulation of active substances.
- Another possibility was disclosed by Carter (US 2012/0277416), where phospholipids were bound to the ending anomeric center of HA oligomer.
- a derivative of an oligomer having an amine in the position 1 was prepared by means of reductive amination, then it was conjugated with an active carboxylic group of a phospholipid.
- the resulting conjugates exhibited a wide range of biological activities.
- a similar procedure of bonding to a HA oligomer having an amino group at the reduced anomeric end was published by Siiskonen in 2013, where a mark 2-aminoacridon was bound. Said conjugate was used for studying the biodistribution of hyaluronan fragments in cytosol.
- a drawback of the above mentioned methods is the fact that they allow the formation of conjugates of HA oligomers or polymers which do not allow their further release in the native form.
- the cause thereof is the fact that all up-till-now known methods of bonding amines to the ending anomeric center are associated with the reduction, i.e. with an irreversible modification of the ending cycle which remains permanently open and does not allow the reverse release of the oligomer in the native form.
- the situation is illustrated by the following Scheme 1:
- the subject-matter of the invention is the conjugate of an oligomer of hyaluronic acid or of a salt thereof according to any of the general I, II, III or IV,
- the structure of the resulting conjugates depends to a great extent on the character of the substitute X. If X is an oxygen bridge —O—, an imino form is significantly present. If X is a nitrogen bridge —NH—, the dominant form is an amino having the beta configuration.
- the residue of hyaluronic acid oligomer in the conjugate according to this invention has 1 to 17 saccharidic cycles, wherein the saccharidic cycle is selected from the group consisting of ⁇ -(1,3)-D-glucuronic acid and ⁇ -(1,4)-N-acetyl-D-glucosamine.
- the conjugates of hyaluronic acid oligomer of the general formulae I and II defined above may be prepared by the method of the invention, the subject-matter of which is that in the first step an oligomer of hyaluronic acid reacts on its ending anomeric center in the position 1 with an excess of a diamino linker of the general formula H 2 N—X—R 5 —X—NH 2 , where R 5 is selected from the group comprising C 1 -C 30 alkyl, C 1 -C 30 alkylaryl, or C 1 -C 30 alkylheteroaryl which optionally comprises one or more identical or different heteroatoms selected from the group comprising N, O, S, and X is O or NH group; in a slightly acid environment at the pH within the range 3 to 6.99, preferably at pH within the range 3 to 6, more preferably 5 to 6, whereafter the conjugates of hyaluronic acid oligomer-diamino linker of the general formulae
- the reaction takes place at an excess of the diamino linker which statistically eliminates significantly the modification at both ends of the linker.
- the slightly acidic environment having the pH within the range 3 to 6.99 is achieved by an addition of a carboxylic acid to the reaction medium, preferably acetic acid, propanoic acid or lactic acid, more preferably acetic acid.
- a carboxylic acid preferably acetic acid, propanoic acid or lactic acid, more preferably acetic acid.
- the amount of the acid is within the range of 5 to 30 equivalents, preferably within the range of 10 to 15 equivalents, with respect to the molar amount of the disaccharide of hyaluronic acid as a substrate.
- the amount of the diamino linker is within the range of 5 to 30 equivalents, preferably 10 equivalents, with respect to the molar amount of the disaccharide of hyaluronic acid as a substrate.
- the first step proceeds at the temperature of 10 to 40° C., preferably at the temperature of 20° C., for 24 to 150 hours, preferably 60 to 80 hours.
- the second step of the reaction takes place, in which the conjugates of the hyaluronic acid oligomer-diamino linker of the general formulae V and VI, as defined above, are reacted with at least one aldehydic group of the substrate in water or in a mixture of water and a water-miscible organic solvent which is selected from the group comprising ethanol, isopropanol, methanol or dimethylsulfoxide.
- the second step is carried out at the temperature of 10 to 40° C. as well, preferably at 20° C., for 24 to 150 hours, preferably 60 to 80 hours.
- conjugates of the oligomer of hyaluronic acid-diamino linker according to the general formula V and VI, as defined above are reacted, according to the method and conditions as stated above, with at least one aldehydic group of the substrate in the presence of a reducing agent which is preferably selected from the group comprising cyano borohydride (NaBH 3 CN) or picoline borane, to form conjugates of the general formulae III and IV, where the substrate is bound by a hydrolytically very strong bond.
- a reducing agent which is preferably selected from the group comprising cyano borohydride (NaBH 3 CN) or picoline borane
- the amount of the reducing agent is within the range of 0.1 to 5 equivalents, preferably 3 equivalents, with respect to the molar amount of the hyaluronic acid disaccharide.
- the conjugate according to this invention allows the release:
- HA oligomers exhibit the biological activity for example to cancer cells.
- the prepared systems exhibited an enhanced biological activity against selected lines of cancer cells.
- the conjugates of the general formulae I to IV, as defined above are preferably used as carriers of biologically active oligomers in pharmacy and biomedicine, or it is possible to use them for the preparation of materials having an anticancer effect.
- pharmaceutically acceptable salt means salts of HA conjugates according to the invention, which are safe and effective for an in vivo use and have the desired biological activity.
- the pharmaceutically acceptable salts include preferably ions of alkali metals or alkaline earth metals, more preferably Na + , K + , Mg + or Li + .
- polysaccharide means a polysaccharide, such as hyaluronic acid, a pharmaceutical salt thereof, starch, glycogen, cellulose etc., which contain at least one aldehydic group after the oxidation of their OH groups.
- conjugate means a compound which is formed by bonding of two or more chemical compounds by means of a covalent bond.
- the conjugate according to this invention is formed by bonding a HA oligomer and a linker giving rise to a conjugate HA oligomer-linker and then by bonding thereof to a substrate, i.e. a polysaccharide, preferably hyaluronic acid, while forming the conjugate HA oligomer-linker-substrate.
- oligomer of hyaluronic acid means an oligomer of hyaluronic acid containing alternately repeating saccharidic cycles ⁇ -(1,3)- D -glucuronic acid and ⁇ -(1,4)-N-acetyl- D -glucosamine.
- the number of saccharidic cycles is 2 to 18.
- the residue of hyaluronic acid oligomer means at least one saccharidic cycle of hyaluronic acid oligomer, which is ⁇ -(1,4)-N-acetyl- D -glucosamine or ⁇ -(1,3)- D -glucuronic acid.
- said one saccharidic cycle is ⁇ -(1,4)-N-acetyl- D -glucosamine.
- the ending saccharidic cycle bonded to the linker via its anomeric center is ⁇ -(1,4)-N-acetyl- D -glucosamine
- said one saccharidic cycle is ⁇ -(1,3)- D -glucuronic acid.
- the saccharidic cycles of ⁇ -(1,3)- D -glucuronic acid and f ⁇ -(1,4)-N-acetyl- D -glucosamine are repeated alternately.
- excess means an amount of diamino linker which is higher than one equivalent with respect to the molar amount of hyaluronic acid disaccharide as a substrate.
- reaction mixture is neutralised and the precipitated reaction product is filtered off and dried.
- FIG. 1 shows the course of inhibition of the growth of the imortalized cancerogenic cells in percents of the non-affected control.
- eq equivalent (eq) used herein relates to a disaccharide of hyaluronic acid, if not indicated otherwise.
- the percents are meant to be weight percents, if not indicated otherwise.
- the molecular weight of the initial hyaluronic acid (source: CPN spol. s r.o., Dolni Dobrou ⁇ , CZ) is a weight average molecular weight within the range of 10 4 to 10 6 g ⁇ mol ⁇ 1 and was measured by SEC-MALLS.
- Hyaluronic acid oligomers comprising 2 to 18 saccharidic cycles were prepared by an enzymatic degradation of the polymer having a higher molecular weight.
- aqueous NaClO solution (0.5 eq) was gradually added to a one-percent aqueous solution of hyaluronan (1 g, 200 kDa), containing NaCl 1%, TEMPO (0.01 eq) and NaHCO 3 (5 eq.), under the nitrogen atmosphere.
- the mixture was stirred for 12 hours at the temperature of 0° C., then 0.1 g of ethanol was added and the mixture was stirred for another 1 hour.
- HA octasacharide was dissolved in water in a concentration of 5%. Then dihydrazide adipate (6 equivalents) and acetic acid (15 equivalents) were added and the mixture was stirred at the temperature of 20° C. for 72 hours at pH 4. The resulting mixture was neutralised with NaHCO 3 and repeatedly precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- HA trisaccharide (ending with glucuronic acid) was dissolved in water in the concentration of 7%. Then dihydrazide adipate (25 equivalents) and acetic acid (25 equivalents) were added and the mixture was stirred at the temperature of 10° C. for 150 hours at pH 6. The resulting mixture was neutralised by NaHCO 3 and repeatedly precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- HA octadecasaccharide (ending with glucosamine) was dissolved in water in the concentration of 5%. Then dihydrazide adipate (15 equivalents) and acetic acid (20 equivalents) were added and the mixture was stirred at the temperature of 40° C. for 24 hours at pH 5. The resulting mixture was neutralised by NaHCO 3 and repeatedly precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- HA decasaccharide was dissolved in water in the concentration of 3%. Then O,O′-4,3-propane diylbishydroxyl amine (5 equivalents) and lactic acid (5 equivalents) were added and the mixture was stirred at the temperature of 20° C. for 100 hours at pH 6. The resulting mixture was neutralised by NaHCO 3 and repeatedly precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- HA tetrasaccharide was dissolved in water in the concentration of 3%. Then terephthaloyl dihydrazide (5 equivalents) and propanoic acid (6 equivalents) were added and the mixture was stirred at the temperature of 20° C. for 100 hours at pH 6. The resulting mixture was neutralised by NaHCO 3 and repeatedly precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- Example 7 Bonding of the Conjugate HA-8 Dihydrazide Adipate (Example 2) to Hyaluronan Oxidised in the Position 6 to an Aldehyde (Example 1) by Reductive Amination
- DOSY NMR (D 2 O) ⁇ 4.24 (d, J 9.7 Hz, 1H, —O—CH—NH— beta) has the same mobility as hyaluronic acid having a higher molecular weight and signals of diastereotopic hydrogens of 2.85 a 3.12.
- Example 8 Bonding of the Conjugate HA-3 Dihydrazide Adipate (Example 3) to Hyaluronan Oxidised in the Position 6 to an Aldehyde (Example 1) by Reductive Amination
- DOSY NMR (D 2 O) ⁇ 4.11 (d, J 8.8 Hz, 1H, —O—CH—NH— beta) has the same mobility as hyaluronic acid having a higher molecular weight and signals of diastereotopic hydrogens of 2.89 a 3.04.
- Example 9 Bonding of the Conjugate HA-8 Dihydrazide Adipate (Example 2) to Hyaluronan Oxidised in the Position 6 to an Aldehyde (Example 1) without Reduction
- 0.1 g of the conjugate prepared according to Example 2 were dissolved in a mixture of water/DMSO in the ratio 1/1 in the concentration of 2%. Then 0.1 g of the derivative of hyaluronic acid containing an aldehyde (molecular weight 2 ⁇ 10 4 g ⁇ mol ⁇ 1 ) was added. The mixture was stirred at the temperature of 20° C. for 72 hours. The resulting mixture was precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- DOSY NMR (D 2 O) ⁇ 4.24 (d, J 9.7 Hz, 1H, —O—CH—NH— beta) has the same mobility as hyaluronic acid having a higher molecular weight and the signal 7.48.
- Example 10 Bonding of the Conjugate HA-18 Dihydrazide Adipate (Example 4) to Hyaluronan Oxidised in the Position 6 to an Aldehyde (Example 1) without Reduction
- 0.1 g of the conjugate prepared according to Example 4 were dissolved in water in the concentration of 2%. Then 0.1 g of the derivative of hyaluronic acid containing an aldehyde (molecular weight 2 ⁇ 10 4 g ⁇ mol ⁇ 1 ) was added. The mixture was stirred at the temperature of 10° C. for 100 hours. The resulting mixture was precipitated by means of isopropyl alcohol. The final solid product was dried in vacuum.
- DOSY NMR (D 2 O) ⁇ 4.25 (d, J 9.7 Hz, 1H, —O—CH—NH— beta) has the same mobility as hyaluronic acid having a higher molecular weight and the signal 7.47.
- Example 11 Bonding of the Conjugate HA-10-O,O′′-1,3-Propane Diylbishydroxyl-Amine (Example 5) to Hyaluronan Oxidised in the Position 6 to an Aldehyde (Example 1) without Reduction
- the cell line cultured at standard conditions (medium DMEM with 10% FBS, 37° C., 5% CO 2 ) was seeded into 4 96-wells culture panels in the density of 5000 cells per a well and incubated in 200.1 of the medium for 24 hours. Thereafter, the culture medium was exchanged for a fresh medium containing the conjugate (Example 8) in concentrations 1000, 100 and 10 ⁇ g/ml. The medium for the control cells was exchanged for a fresh one without the conjugate. Immediately after the treatment, the cell viability was measured in the first panel by means of the MTT method. In brief, 20 ⁇ l of the MTT solution (5 mg/ml) were added to the cells and together they were incubated for 2.5 hours in dark at 37° C.
- the culture medium was sucked off and the cell monolayer was lysed by a mixture of DMSO and isopopanol (1:1) with 10% Triton X-100.
- the resulting colour in individual wells of the panel was measured by means of a plate spectrophotometer (absorbance at 570 nm with the correction at 690 nm). This measurement was repeated at the other panels as well every 24 hours.
- the final viability was calculated as the ratio of the absorbance of the sample in a given time and in time T0.
- A2058 is an immortalised cell line derived from the human melanoma, it is very invasive and for that reason, it is often used as a model of tumorigenesis and metastasizing.
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CZ2014150A3 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
CZ2015398A3 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
WO2020085734A1 (ko) * | 2018-10-24 | 2020-04-30 | 주식회사 화이바이오메드 | 히알루론산 말단의 알데하이드 그룹을 이용하여 제조한 약물 접합체 |
US20220213233A1 (en) * | 2019-04-19 | 2022-07-07 | Jointherapeutics S.R.L. | Crosslinked polymer of functionalized hyaluronic acid and its use in the treatment of inflammatory states |
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